How To Muster Your Confidence And Tell Someone You Like Them

My romantic history reads like Cliff Notes from all of Shakespeare’s tragedies. And most of his comedies. Not entirely successful then, with a smattering of jealousy, and rejection by the ladle full.

But hey, at least I give it a go, right?

Taking that first step and telling someone that you want to be more than “just friends” is about as scary as it gets, and those heart-thumping moments before you open yourself up can be enough to make you turn on your heels and flee.

Turning and fleeing aren’t conducive to a good relationship though (I’ve learned that), so here’s how to tell someone you like them in 12 simple steps.

1. Wait for the right opportunity

Asking someone out through the bathroom door or telling someone you like them during a business meeting aren’t the best way to go. To have this work, it’s best if you’re both relaxed and have a little privacy, and it’s a great idea if you’re both engaged in some kind of activity, whether it’s sipping a coffee, taking a walk, or seeing a show.

Think about when and where you’ll each be feeling good, then get to it.

2. Don’t wait for the right opportunity forever

There’s no such thing as the “perfect time,” and people miss all kinds of opportunities and moments because they’re waiting around for a time that’s just a “little more right.”

Finding an imperfect moment to ask someone out is always better than waiting for a moment that never comes.

3. Take the drama out of it

Your heart thumps, your palms sweat, your stomach flutters, and adrenalin hits. It feels like a big deal, and all of the drama surrounding the moment you tell someone how you feel only adds more weight and pressure. Weight and pressure that you don’t need.

So lighten up a little and reassure yourself. The sun will rise again tomorrow. You’re not going to die. Whatever happens, this will be okay.

4. Don’t project forwards

Stories have been part of human culture for as long as we’ve been around, and you’re hardwired to spin them. They help you make sense of the world and everything in it, and it’s through the stories you weave that you figure out what things mean to you and how you react to them.

You might fall in love, get married, and grow old together. You might end up divorced and hating each other. What if you fall for them and they end up stamping all over your heart? What if you let them down?

None of these stories matter. They’re all fiction. What does matter is your next choice.

5. Take a look at your motivation

What’s the reason you want to tell them you like them? Is it because you get all lit up and fuzzy when you’re around them? Is it because you like who you are when you’re with them? Or is it because they give you validation that’s as moreish as chocolate brownies made of kisses?

Don’t tell them you like them because of what they can give you. Do it because you want to share more with them, because you love who they are, and because you’re curious about what you could be to each other.

6. Accept that it will be uncomfortable

There’s no way to tell someone you like them without a little discomfort. The very essence of this means that you’re putting something on the line and taking a risk—and inherent in risk-taking is going out of your comfort zone.

So don’t beat on, or get hung up on feeling awkward or uncomfortable—it’s simply part of the process. Vulnerability requires discomfort, and that’s just as it needs to be.

7. Feeling nervous doesn’t mean you’re not confident

When those nerves kick in, it’s easy to believe that you’re not up to the task or can’t do it. The experience of feeling nervous takes over, and you forget all about the natural confidence you have in your bones.

But nerves don’t preclude confidence any more than wearing a size 42 shoe precludes you from going barefoot.

Those nerves mean you’re doing something new and something that matters, and trusting yourself to make a choice within that experience is confidence.

8. Share something that matters

A relationship is nourished through sharing. Sounds glib and overly simplistic, but it’s true. Perhaps especially so at the start.

You can share something of yourself—a story, a hope or a passion. You can share something with them because it made you think of them—a book you think they’ll love, a place you think they’ll enjoy, or a song that brought them to mind. Or you can share a moment in time—a great view, laughing ’til you cry, or a moment of pure indulgence.

Sharing something that matters makes opening up feel natural.

9. How would the “confident you” do this?

In the moment you feel your confidence vanish, pause for a moment and ask yourself how that version of you who’s flowing, buzzing, at the top of their game, and firing on all cylinders would do this.

When you’re at your best there’s a sense of ease and flow that makes things so much more simple. You don’t question whether you can or can’t, you just do. You don’t question whether you should or shouldn’t, you just engage. You don’t question whether you’re good enough or worthy enough, you accept that you’re plenty.

That version of you at your best—the you who’s naturally confident—is always there. You just have to remind yourself from time to time.

10. Say, “Hey,” to the elephant in the room

Rejection. There, I said it! As much as you might not like to entertain the idea, and as horrible as the anticipation of it feels, it’s a real possibility.

The fact that someone might turn you down, say no to that date, or reject your advances is enough to stop many of us in our tracks. But you should always remember that their choices are theirs to make, and should they turn you down it’s not a judgment about your worth, it’s only about their tastes, their circumstances, and their story.

Rejection is not the enemy. Not taking the risk to be rejected is what you should be scared of.

11. Don’t worry about the words

But just as there’s no perfect time, there’s no such thing as the perfect thing to say. You don’t need a Hollywood “You complete me,” “You make me want to be a better man,” or “I’m just a girl, standing in front of a boy, asking him to love her.” All you need is to trust the words that reach your lips—stutters, stumbles, stammers, and all.

12. Keep it simple

It’s tempting to engineer a place, time, or specific set of circumstances that will make telling someone you like them easy and natural, when in reality all of those thoughts and expectations just make things more difficult and complex.

So keep it simple. Don’t overengineer it. Don’t create a huge chain of dependencies that have to be true in order for you to say what you want to say. Don’t turn this into struggle with yourself.

A simple, “Hey, want to grab a coffee with me tomorrow?” might be all that’s needed, so be sure to choose ease and simplicity over struggle and complexity.

At the end of the day, there’s probably just one thing to ask yourself: Do you want to be the kind of person who turns away from possibility, or the kind of person who gave it a shot just because something amazing might happen?

Steve's a confidence coach who helps you build confidence so you can get out there and do what matters to you in ways that work for you. Grab The Code, build your natural confidence and go dent the universe.